The slow, sustained release of an active ingredient is a highly desirable trait in many personal care, textile, automotive, plastic, laundry and household products. A number of means have been proposed and implemented to achieve this goal. Among these means are dissolving or suspending fragrant compounds in personal care emulsions (U.S. Pat. Nos. 5,525,588; 5,525,555; 5,490,982; 5,372,806; EP 0334490; WO 0064497), encapsulation of a fragrant compound (U.S. Pat. Nos. 5,500,223; 5,324,444; 5,185,155; 5,176,903; 5,130,171; 6,325,859; 6,309,715; 6,325,274; 6,213,409; 6,200,949; 6,042,792; 5,867,755; 5,049,182 6,624,136; U.S. patent applications 20020187221, 20020009522, and 20010008635; EP 1116515, EP 1061124, EP 1133929; WO 0179303, WO 0173188A1, WO 9815192A1, WO 02076514), dissolving a fragrant compound into a hydrophobic phase such as a silicone (U.S. Pat. Nos. 5,449,512; 5,160,494; 5,234,689; WO 0241709A1), incorporation of a fragrant compound into crosslinked polymers (U.S. Pat. Nos. 6,435,423; 5,139,864; 6,379,689; 5,387,622; 5,387,411; WO 03032749; WO 02065858; JP 11047581), incorporation of fragrant compounds into permeable laminates (U.S. Pat. Nos. 6,500,444; 5,071,704; 5,008,115), incorporation of fragrant compounds into matrices that soften at body temperature (U.S. Pat. No. 4,908,208; EP 1178107; WO 0016643), incorporation of fragrant compounds into matrices that biodegrade (U.S. Pat. No. 6,121,343) or are bioactivated (U.S. Pat. No. 5,378,468), incorporation of fragrant compounds into rate controlling membranes (U.S. Pat. Nos. 6,063,365 and 4,445,641), and derivatization of silanes with fragrant alcohols to form alkoxy silanes (U.S. Pat. Nos. 4,524,018 and 4,500,725), derivatization of fragrances to form photosensitive molecules that release the fragrance upon exposure to light (WO 02083620; JP2002020783A). Derivatization of actives to give hydrolyzable organic (i.e., not containing silicon) molecules has also been well documented in the literature.
The marriage of silicon-containing molecules with active ingredients is of particular interest since many active ingredients are highly functional organics and suffer from incompatibility with the silicones that are found in personal and consumer care products, leading to syneresis and other phase separation phenomena. Derivatization of silanes with long-chain alcoholic skin care actives to give alkoxytrimethysilanes (U.S. Pat. No. 5,847,179) and derivatization of silanes with hydroxycarboxylic acid skin exfoliants to form (triorganosilyl)alkoxycarboxylates (U.S. Pat. Nos. 6,143,309; 6,228,380; 6,267,977) have been described. Direct displacement of an alkoxy leaving group on a silicon atom by a fragrant alcohol was reported by Allen, et al. to give fragrant silicon esters or linear silicate esters (U.S. Pat. Nos. 3,215,719 and 3,271,305). Several others also reported similar alkoxy displacement reaction to form linear fragrant siloxane polymers or copolymers (GB 2,041,964; GB 2,042,890; EP 273266). Reaction of an alcohol, aldehyde, ketone or lactone with a silyl hydride in the presence of a metal carboxylate salt and a reducing agent to form linear polymers and copolymers was also reported (WO 9628497). Other routes to fragrant silicones using silyl hydrides were disclosed by Anderson, et al. (EP 878497, JP 10330382, U.S. Pat. No. 6,262,287) and Perry, et al. (U.S. Pat. Nos. 6,046,156; 6,077,923; 6,153,578; 6,054,547; 6,075,111; 6,322,777; 6,083,901). In these processes, hydrosilylation chemistry was employed to join the active portion of the molecule to the silicone backbone. What is not taught or suggested by the prior art is the formation and use of active ingredient-functional cyclic siloxane compositions for personal care, textile, laundry or plastics applications. Herein we disclose a new composition and method for preparation of active ingredient functional cyclic siloxane articles from cyclic silyl hydrides. The method is the direct reaction of an alcohol- or carbonyl-containing compound with the cyclic silyl hydride in the presence of a catalyst to generate the product and hydrogen gas byproduct.